Dimethylformamide → 2-(2-Aminoethyl)-3,5-di-tert-butylphenol
Reaction equation
[C:1]([C:5]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:9]([OH:17])[C:6]=1[CH:7]=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(Br)C1C=CC=CC=1.[CH3:28][N:29](C=O)C>>[NH2:29][CH2:28][CH2:7][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][C:9]=1[OH:17]Participants
Procedure
To a solution of 1.17 g (5.0 mmol) of 2,4-di-tert-butyl-6-hydroxybenzaldehyde (from Step A of Example 35) in 10 mL of dry DMF was added 0.25 g (10.4 mmol) of powdered sodium hydride and the resulting mixture was stirred for 30 min under a nitrogen atmosphere. Benzyl bromide (1.0 g, 5.9 mmol) was then added and the resulting mixture was stirred for an additional 3 h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between ether and water. The aqueous layer was re extracted with ether and the organic layers were then combined, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0-10% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.
Workup
- stirringthe resulting mixture was stirred for an additional 3 h
- concentrationThe reaction mixture was then concentrated in vacuo
- customthe residue was partitioned between ether and water
- extractionThe aqueous layer was re extracted with ether
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe residue was purified on a silica gel flash chromatography column
- washeluted with 0-10% EtOAc-hexane
- customCombination of the purified fractions and drying in vacuo
Sources & evidence
- ORD record
- ord-fedf4424c9da40b2972b560d32d601d4
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589127B2
Reaction notes
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